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Updated: Jul 6, 2025

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
Phototriggered Butenolide Formation from a Cyclobutenedione and an Acidic Nucleophile
Kenji Mishiro1, Aiko Sesumi2, Takanori Fujii2
1Institute for Frontier Science Initiative, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan.
Abstract:
A phototriggered conjugation reaction of an aminocyclobutenedione and an acidic nucleophile was discovered. Upon blue light irradiation of the materials, a butenolide derivative with substituents derived from the aminocyclobutenedione and the nucleophile was produced. The reaction proceeded efficiently under organic solvent or organic solvent/aqueous buffer (1/1) conditions. This reaction would be useful for the synthesis of unique butenolide derivatives and derivatization of acidic functional groups contained in aqueous biomolecules.
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